ETHYLENE DIAMINE (ETLEN DAMN) (EDA)
ETHYLENE DIAMINE
ETHYLENE DIAMINE; EDA; ethylene diamine; ethylen diamine; ethylene diamin; ethylen diamine; etilen diamin; ethylenediamine; Ethane-1,2-diamine; 1,2-Ethanediamine; 107-15-3; 1,2-Diaminoethane; Ethylene diamine; Ethylendiamine; edamine; Dimethylenediamine; 1,2-Ethylenediamine; Aethaldiamin; Aethylenediamin; Ethyleendiamine; Ethylene-diamine; beta-Aminoethylamine; 1,2-Diaminoaethan; Algicode 106L; Amerstat 274; 1,2-Diamino-ethaan; 1,2-Diamino-ethano; Aethaldiamin [German]; Caswell No. 437; Ethylenediamine [JAN]; Ethyleendiamine [Dutch]; 1,2-Ethanediamine, homopolymer; Aethylenediamin [German]; Ethylene-diamine [French]; NCI-C60402; UNII-60V9STC53F; 1,2-Diaminoaethan [German]; 1,2-Diamino-ethaan [Dutch]; CCRIS 5224; ETHYLENEDIAMINE ANHYDROUS; HSDB 535; 1,2-Diamino-ethano [Italian]; CHEBI:30347; Aminophylline Injectio; Ethylenediamine, p0iperazine Polymer; EINECS 203-468-6; UN1604; CHEMBL816; H2NCH2CH2NH2; EPA Pesticide Chemical Code 004205; BRN 0605263; ETHANE,1,2-DIAMINO; Ethylendiamin; AI3-24231; 60V9STC53F; 2-Aminoethylammonium chloride; MFCD00008204; 1, 2-Diaminoethane; 27308-78-7; Ethylenediamine [UN1604] [Corrosive]; Ethylenediamine, 99%; NCGC00091527-01; Ethylenediamine, 99+%; DSSTox_CID_1881; DSSTox_RID_76382; 1,2-diaminoethane phase II; DSSTox_GSID_21881; 1,2-diaminoethane phase I beta; 1,2-diaminoethane phase I alpha; Polyamines; Ethylenediamine, 99+%, AcroSeal(R); CAS-107-15-3; Ethylenediamine, ReagentPlus(R), >=99%; 1,2-Ethanediamine, monohydrochloride; 1,2-Ethanediamine, hydrochloride (1:1); Ethylenediamine [USP:JAN]; ethylenediarnine; 2-aminoethylamine; ethylene di amine; 1,4-diazabutane; 1,2-diaminoethan; ethylene – diamine; 1,2-ethylendiamine; Edamine [INN]; 1,2-diamino-ethane; ethane 1,2-diamine; N,N’-ethylenediamine; Ethylenediamine, 8CI; 1,2-ethylene diamine; 1,2-ethylene-diamine; .beta.-Aminoethylamine; ethane-1, 2-diamine; Ethylenediamine solution; N,N’-ethylene diamine; ACMC-1BOEG; Ethylenediamine, BioXtra; Epitope ID:117724; EC 203-468-6; 4-04-00-01166 (Beilstein Handbook Reference); KSC178S6D; Ethylenediamine (USP/JP15); Ethylenediamine (USP/JP17); [N]CC[N]; BDBM7972; NH2(CH2)2NH2; 624-59-9 (di-hydrobromide); 333-18-6 (di-hydrochloride); 5700-49-2 (di-hydriodide); Ethylenediamine, analytical standard; Ethylenediamine, for synthesis, 99.0%; Ethylenediamine [UN1604] [Corrosive]; Ethylenediamine solution, technical, 75-80%; Ethylenediamine, SAJ special grade, >=99.0%; 25469-EP2289881A1; 25469-EP2295436A1; 25469-EP2298762A2; 25469-EP2298773A1; 25469-EP2305808A1; 25469-EP2308852A1; 25469-EP2314580A1; Ethylenediamine, meets USP testing specifications; 167669-EP2272813A2; 167669-EP2275395A2; 167669-EP2281563A1; Ethylenediamine, Vetec(TM) reagent grade, >=98%; Q411362; J-001723; Ethylenediamine, purified by redistillation, >=99.5%; F2191-0279; Ethylenediamine, puriss. p.a., absolute, >=99.5% (GC); QuadraPure(R) AEA, 100-400 mum particle size, extent of labeling: 1.3 mmol/g loading, 1 % cross-linked with divinylbenzene
ETHYLENE DIAMINE
CAS : 107-15-3
Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a strongly basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998.[6] Ethylenediamine readily reacts with moisture in humid air to produce a corrosive, toxic and irritating mist, to which even short exposures can cause serious damage to health (see safety). Ethylenediamine is the first member of the so-called polyethylene amines. Ethylenediamine is produced industrially by treating 1,2-dichloroethane with ammonia under pressure at 180 °C in an aqueous medium:Ethylendiamin In this reaction hydrogen chloride is generated, which forms a salt with the amine. The amine is liberated by addition of sodium hydroxide and can then be recovered by rectification [de]. Diethylenetriamine (DETA) and triethylenetetramine (TETA) are formed as by-products. Another industrial route to ethylenediamine involves the reaction of ethanolamine and ammonia This process involves passing the gaseous reactants over a bed of nickel heterogeneous catalysts. Ethylenediamine can be purified by treatment with sodium hydroxide to remove water followed by distillation. Ethylenediamine is used in large quantities for production of many industrial chemicals. It forms derivatives with carboxylic acids (including fatty acids), nitriles, alcohols (at elevated temperatures), alkylating agents, carbon disulfide, and aldehydes and ketones. Because of its bifunctional nature, having two amines, it readily forms heterocycles such as imidazolidines.
Precursor to chelation agents, drugs, and agrochemicals
A most prominent derivative of ethylenediamine is the chelating agent EDTA, which is derived from ethylenediamine via a Strecker synthesis involving cyanide and formaldehyde. Hydroxyethylethylenediamine is another commercially significant chelating agent.[6] Numerous bio-active compounds and drugs contain the N-CH2-CH2-N linkage, including some antihistamines.[10] Salts of ethylenebisdithiocarbamate are commercially significant fungicides under the brand names Maneb, Mancozeb, Zineb, and Metiram. Some imidazoline-containing fungicides are derived from ethylenediamine.
Pharmaceutical ingredient
Ethylenediamine is an ingredient in the common bronchodilator drug aminophylline, where it serves to solubilize the active ingredient theophylline. Ethylenediamine has also been used in dermatologic preparations, but has been removed from some because of causing contact dermatitis. When used as a pharmaceutical excipient, after oral administration its bioavailability is about 0.34, due to a substantial first-pass effect. Less than 20% is eliminated by renal excretion. Ethylenediamine-derived antihistamines are the oldest of the five classes of first-generation antihistamines, beginning with piperoxan aka benodain, discovered in 1933 at the Pasteur Institute in France, and also including mepyramine, tripelennamine, and antazoline. The other classes are derivatives of ethanolamine, alkylamine, piperazine, and others (primarily tricyclic and tetracyclic compounds related to phenothiazines, tricyclic antidepressants, as well as the cyproheptadine-phenindamine family)
Ethylene Diamine’s Role in polymers
Ethylenediamine, because it contains two amine groups, is a widely used precursor to various polymers. Condensates derived from formaldehyde are plasticizers. It is widely used in the production of polyurethane fibers. The PAMAM class of dendrimers are derived from ethylenediamine.
Other applications of Ethylene diamine
-as a solvent, it is miscible with polar solvents and is used to solubilize proteins such as albumins and casein. It is also used in certain electroplating baths.
-as a corrosion inhibitor in paints and coolants.
-ethylenediamine dihydroiodide (EDDI) is added to animal feeds as a source of iodide.
-chemicals for color photography developing, binders, adhesives, fabric softeners, curing agents for epoxies, and dyes.
-as a compound to sensitize nitromethane into an explosive. This mixture was used at Picatinny Arsenal during WWII, giving the nitromethane and ethylenediamine mixture the nickname PLX, or Picatinny Liquid Explosive.
Coordination chemistry
Ethylenediamine is a well-known bidentate chelating ligand for coordination compounds, with the two nitrogen atoms donating their lone pairs of electrons when ethylenediamine acts as a ligand. It is often abbreviated “en” in inorganic chemistry. The complex [Co(ethylenediamine)3]3+ is an archetypical chiral tris-chelate complex. The salen ligands, some of which are used in catalysis, are derived from the condensation of salicylaldehydes and ethylenediamine.
Related ligands
Related derivatives of ethylenediamine include ethylenediaminetetraacetic acid (EDTA), tetramethylethylenediamine (TMEDA), and tetraethylethylenediamine (TEEDA). Chiral analogs of ethylenediamine include 1,2-diaminopropane and trans-diaminocyclohexane.
Safety
Ethylenediamine, like ammonia and other low-molecular weight amines, is a skin and respiratory irritant. Unless tightly contained, liquid ethylenediamine will release toxic and irritating vapors into its surroundings, especially on heating. The vapors react with moisture in humid air to form a characteristic white mist, which is extremely irritating to skin, eyes, lungs and mucus membranes.
Ethylenediamine is an organic compound that is used as a building block for the production of many other chemical products. It is also used as an excipient in many pharmacological preparations such as creams. Notably, ethylenediamine is a contact sensitizer capable of producing local and generalized reactions 1. Sensitivity to ethylenediamine may be identified with a clinical patch test.
Application of Ethylene Diamine
Ethylenediamine (en) has been used in the following process:
• Synthesis of nucleus pulposus (NP)-like collagen-glycosaminoglycans (CG) core.
• Surface modification of epoxy-activated cryogel.
• Alteration of the surface of carbon nanoparticles (CNPs) to generate CNPs-ethylene.
It may be used in the following studies:
• Surface modification of triazolate-bridged metal-organic framework.
• As a solvent in the synthesis of ZnS (zinc sulfide) and ZnSe (zinc selenium) precursors by solvothermal process.
• As a reactant in the synthesis of Pd/C-ethylenediamine complex catalyst.
• As a chelating agent in the synthesis of β-Co(OH)2 nanocrystals.
• Synthesis of ethylenediamine-templated iron arsenates and fluoroarsenates.
• As a template agent and coordination agent in the synthesis of CdS (cadmium sulfide) nanocrystals.
General description of Ethylene Diamine
Ethylenediamine (en) is a linear aliphatic diamine that can be synthesized by reacting ethanolamine and ammonia in the presence of zeolite catalyst. Its effect as an allergen has been investigated. It participates in the synthesis of metal chalcogenides and thiogallates.
Etilendiamin (bir ligand olduunda en olarak ksaltlr), C2H4 (NH2) 2 formülüne sahip organik bileiktir. Amonyak benzeri bir kokuya sahip bu renksiz sv, güçlü bir bazik amindir. 1998 ylnda üretilen yaklak 500.000 ton ile kimyasal sentezde yaygn olarak kullanlan bir yap tadr. Etilendiamin, ksa süreli maruz kalmalarn bile sala ciddi zararlar verebilecei andrc, toksik ve tahri edici bir sis oluturmak için nemli havadaki nem ile kolayca reaksiyona girer (bkz. Emniyet). Etilendiamin, sözde polietilen aminlerin ilk üyesidir. Etilendiamin, sulu bir ortamda 180 ° C’de basnç altnda 1,2-dikloroetann amonyak ile ilenmesiyle endüstriyel olarak üretilir: Etilendiamin Bu reaksiyonda, amin ile bir tuz oluturan hidrojen klorür üretilir. Amin, sodyum hidroksit ilavesiyle aça çkar ve daha sonra artma [de] ile geri kazanlabilir. Yan ürünler olarak dietilentriamin (DETA) ve trietilentetramin (TETA) oluturulur. Etilendiamine giden baka bir endüstriyel yol, etanolamin ve amonyan reaksiyonunu içerir. Bu ilem, gaz halindeki reaktanlarn bir nikel heterojen katalizör yata üzerinden geçirilmesini içerir. Etilendiamin, suyu uzaklatrmak için sodyum hidroksit ile ilenip ardndan damtma yoluyla saflatrlabilir. Etilendiamin, birçok endüstriyel kimyasaln üretiminde büyük miktarlarda kullanlmaktadr. Karboksilik asitler (ya asitleri dahil), nitriller, alkoller (yüksek scaklklarda), alkilleme maddeleri, karbon disülfür ve aldehitler ve ketonlarla türevler oluturur. ki amine sahip olan iki ilevli doas nedeniyle, imidazolidin gibi heterosiklleri kolaylkla oluturur.
elasyon ajanlarnn, ilaçlarn ve zirai kimyasallarn öncüsü
Etilendiaminin en belirgin türevi, siyanür ve formaldehit içeren bir Strecker sentezi yoluyla etilendiaminden türetilen kenetleme maddesi EDTA’dr. Hidroksietiletilendiamin, ticari olarak önemli bir kenetleme maddesidir. Çok sayda biyoaktif bileik ve ilaç, baz antihistaminikler dahil olmak üzere N-CH2-CH2-N balantsn içerir. Etilenbisdithiocarbamate tuzlar, Maneb, Mancozeb, Zineb ve Metiram markalar altnda ticari olarak önemli fungisitlerdir. Baz imidazolin içeren fungisitler, etilendiaminden türetilir.
Farmasötik içerik
Etilendiamin, aktif bileen teofilini çözündürmeye hizmet ettii yaygn bronkodilatör ilaç aminofilinin bir bileenidir. Etilendiamin de dermatolojik preparatlarda kullanlm, ancak bazlarndan kontakt dermatite neden olduu için çkarlmtr. Farmasötik bir eksipiyan olarak kullanldnda, oral uygulamadan sonra biyoyararlanm, önemli bir ilk geçi etkisine bal olarak yaklak 0.34’tür. % 20’den az renal atlmla elimine edilir. Etilendiamin türevi antihistaminikler, 1933 ylnda Fransa’daki Pasteur Enstitüsü’nde kefedilen piperoxan aka benodain ile balayan ve ayrca mepiramin, tripelennamin ve antazolin içeren be birinci nesil antihistaminik snfnn en eskisidir. Dier snflar, etanolamin, alkilamin, piperazin ve dierlerinin türevleridir (öncelikle fenotiyazinler, trisiklik antidepresanlar ve ayrca siproheptadin-fenindamin ailesi ile ilgili trisiklik ve tetrasiklik bileikler)
Polimerlerde Etilen Diaminin Rolü
Etilendiamin, iki amin grubu içerdiinden, çeitli polimerlerin yaygn olarak kullanlan bir öncüsüdür. Formaldehitten türetilen kondensatlar plastikletiricilerdir. Poliüretan elyaf üretiminde yaygn olarak kullanlmaktadr. PAMAM snf dendrimerler, etilendiaminden elde edilir.
Etilen diaminin dier uygulamalar
– bir çözücü olarak, polar çözücülerle karabilir ve albüminler ve kazein gibi proteinleri çözündürmek için kullanlr. Baz elektrokaplama banyolarnda da kullanlr.
-Boya ve soutucularda korozyon önleyici olarak.
-etilendiamin dihidroiyodür (EDDI), bir iyodür kayna olarak hayvan yemlerine eklenir.
– renkli fotorafçlk için kimyasallar, balayclar, yaptrclar, kuma yumuatclar, epoksiler için sertletirme maddeleri ve boyalar.
nitrometan bir patlaycya duyarl hale getiren bir bileik olarak. Bu karm, 2. Dünya Sava srasnda Picatinny Arsenal’de kullanld ve nitrometan ve etilendiamin karmna PLX takma ad veya Picatinny Liquid Explosive verdi.
Koordinasyon kimyas
Etilendiamin, etilendiamin bir ligand görevi gördüünde iki nitrojen atomunun kendi elektron çiftlerini balad, koordinasyon bileikleri için iyi bilinen iki dili kenetleme liganddr. Genellikle inorganik kimyada “en” olarak ksaltlr. [Co (ethylenediamine) 3] 3+ kompleksi, arketipik bir kiral tris-elat kompleksidir. Bazlar katalizde kullanlan salen ligandlar, salisilaldehitlerin ve etilendiaminin younlamasndan elde edilir.
lgili ligandlar
lgili etilendiamin türevleri arasnda etilendiamintetraasetik asit (EDTA), tetrametiletilendiamin (TMEDA) ve tetraetiletilendiamin (TEEDA) bulunur. Etilendiaminin iral analoglar arasnda 1,2-diaminopropan ve trans-diaminosikloheksan bulunur.
Emniyet
Etilendiamin, amonyak ve dier düük moleküler arlkl aminler gibi, cildi ve solunum yolunu tahri edicidir. Skca kapatlmad sürece, sv etilendiamin, özellikle stma srasnda çevresine toksik ve tahri edici buharlar salacaktr. Buharlar, cildi, gözleri, akcierleri ve mukus zarlarn son derece tahri eden karakteristik beyaz bir sis oluturmak için nemli havadaki nemle reaksiyona girer.
Etilendiamin, dier birçok kimyasal ürünün üretimi için yap ta olarak kullanlan organik bir bileiktir. Ayrca kremler gibi birçok farmakolojik preparatta eksipiyan olarak kullanlmaktadr. Etilendiamin özellikle lokal ve genel reaksiyonlar üretebilen bir temas duyarllatrcdr 1. Etilendiamine duyarllk bir klinik yama testi ile belirlenebilir.
Etilen Diamin Uygulamas
Ethylenediamine (en) aadaki süreçte kullanlmtr:
• Nukleus pulposus (NP) benzeri kolajen-glikozaminoglikanlar (CG) çekirdeinin sentezi.
• Epoksi ile aktifletirilen kriyojelin yüzey modifikasyonu.
• CNPs-etilen oluturmak için karbon nanopartiküllerin (CNP’ler) yüzeyinin deitirilmesi.
Aadaki çalmalarda kullanlabilir:
• Triazolat köprülü metal organik çerçevenin yüzey modifikasyonu.
• Solvotermal proses ile ZnS (çinko sülfit) ve ZnSe (çinko selenyum) öncülerinin sentezinde çözücü olarak.
• Pd / C-etilendiamin kompleksi katalizörünün sentezinde reaktif olarak.
• β-Co (OH) 2 nanokristallerin sentezinde kenetleme maddesi olarak.
• Etilendiamin ablonlu demir arsenatlarn ve floroarsenatlarn sentezi.
• CdS (kadmiyum sülfit) nanokristallerinin sentezinde ablon ajan ve koordinasyon ajan olarak.
Etilen Diamin’in genel tanm
Etilendiamin (en), zeolit katalizör varlnda etanolamin ve amonyan reaksiyona girmesiyle sentezlenebilen dorusal bir alifatik diamindir. Alerjen olarak etkisi aratrlmtr. Metal kalkojenitlerin ve tiyogallatlarn sentezine katlr.